In almost 60 years I've only had 2 encounters with pickpockets.
One failed one in Rome last year.
One succesful in Barcelona this year, due to a chain of events
including combination of miscommunication between Helen and myself,
lapse of attention/memory on my part (tiredness? the circumstances?)
and overconfidence. This one wasn't too bad due to insurance and the
fact that Helen had a card that didn't have to be cancelled.
I'm convinced it *could* happen again (might never though), the answer
is to make sure it doesn't matter much.